The days and weeks after a celebrity death tend to fill up with public inquiries. The vaguer the circumstances, the more questions proliferate, lead to investigations, trials, depressing tabloid paydays…. But many fans don’t linger over procedural goings-on or prurient details. Many wonder instead “What if?”—as in, how do we reckon the artistic loss? What projects went uncompleted? What kind of collaborations might have been on the horizon?

And now that Prince has left us, we might wonder about all of the superduos that might have formed had he lived into his sixties and beyond. One collaboration that did bear some fruit during his lifetime came just in time for Prince’s superstar partner, Miles Davis, who died in 1991. During the latter half of the ‘80s, the two formed a bond, based on mutual admiration for each other’s music, of course, as well as for each other’s image and generally uncompromising personality.

In fact, since at least 1982, Davis, writes his biographer Ian Carr, became “almost obsessively interested in the androgynous, multi-talented black pop star… whom he rated very highly as an artist." In the short (almost inaudible) interview clip above, Davis describes Prince as a synthesis of James Brown, Marvin Gaye, Jimi Hendrix, and Charlie Chaplin. He also compared Prince to Sly Stone and Little Richard, writes Carr, and commented, “He’s a mixture of all those guys and Duke Ellington.”

For his part, Prince supposedly saw in Davis an older version of himself. After the two artists met in 1985, they crossed paths several more times in the following years, with Miles appearing onstage to play a solo at a Paisley Park New Year’s Eve benefit and recording a solo on the Prince/Chaka Khan song “Sticky Wicked” in 1988. What’s particularly interesting about Prince and Davis’s musical love affair is that the resulting music played to both artists’ strengths, instead of attempting to meld their styles into something out of character.

Davis’ experiments with ‘80s R&B tropes in his 1986 album Tutu stem from their work together, and the record was originally intended as a Prince collaboration. At the top of the post, you can hear an unreleased track originally written for Tutu called “Can I Play With U?” and featuring Prince’s vocals. Tutu ended up going in a different direction, and received some highly mixed reviews, but it retained much of the spirit of Prince. And for Miles---who since the late sixties had absorbed and transformed influences from so many contemporary styles---this seemed perfectly fitting.

The Tutu collab may not have panned out---Prince was apparently unhappy with the results and scrapped his songs---but the two didn’t give up on each other. On the contrary, much of the music Davis played and recorded at the end of his life was written by Prince. Above, hear one such composition, the suggestively named “Penetration,” in a 1991 performance. Though Prince’s funk roots shine through, it’s also a work very much in Davis’s fusion wheelhouse. Although Davis died before the two could complete their long-awaited collaborative album, we don’t have to wonder “What if?”

Much of the music they wrote together survives in live performances like that above and has circulated in a Davis bootleg titled Miles Davis Plays Prince and a Prince bootleg titled Crucial. Does the music on these recordings live up to the outsized talent and personalities of these two geniuses? Probably not—whatever could? But it shows us the direction Davis would have continued to move in had he lived on, and also gives us a way to think about the significant jazz influences in Prince’s music, a subject rarely discussed but worthy of much more consideration.

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Open Culture editor Dan Colman scours the web for the best educational media. He finds the free courses and audio books you need, the language lessons & movies you want, and plenty of enlightenment in between.